1. Field of the Invention
This invention relates to the oxidation of organic compounds by aqueous hypohalites. More particularly, this invention relates to the oxidation of organic compounds oxidizable by hypohalite ion in a biphasic mixture using phase transfer catalysis.
2. Description of the Prior Art
Various methods are known for oxidizing organic compounds by hypohalite ion. For example, C. Y. Meyers, J. Org. Chem., 26, 1046 (1961), teaches the preparation of benzaldehyde by reacting benzyl alcohol with aqueous, methanolic inorganic hypochlorite. E. S. Wallis and J. F. Lane, Org. Reactions, 3, 267 (1947), teach the Hoffman rearrangement of amides to amines by reacting alkali metal hypohalite and a primary amide in aqueous caustic.
Oxidations catalyzed by quaternary onium salts have been reported by C. M. Starks, J. Amer. Chem. Soc., 93, 195 (1971). There, nonanoic acid was prepared in 91 percent yield by reacting aqueous potassium permanganate with 1-decene in the presence of tricaprylmethylammonium chloride. However, no such catalyzed reaction has been reported where hypohalite ion was the oxidizing agent.